I'm a big fan of Mad Men, which is a tv show about advertising executives in the 1960s. It's very philosophical and also the characters speak in a pretty formal way, like people in a book, which might make it easier to understand.

Maybe you could try Nova. I think you could argue that it's meaningful, philosophical, and historical in its own ways. It's basically a science series, though (but that includes things like archeology, which is obviously tied in with history).